CA1077484A - Derives amino des acides thiazolo (5,4-b) pyridine-6-carboxyliques et de leurs esters - Google Patents

Derives amino des acides thiazolo (5,4-b) pyridine-6-carboxyliques et de leurs esters

Info

Publication number: CA1077484A
Authority: CA; Canada
Prior art keywords: carboxylic acid; hydrogen; ethyl ester; methyl; amino
Prior art date: 1975-03-05
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA246,424A

Other languages

English (en)

Inventor

Theodor Denzel

Hans Hoehn

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-03-05

Filing date

1976-02-24

Publication date

1980-05-13

1975-03-05 Priority claimed from US05/555,512 external-priority patent/US3953461A/en

1975-05-12 Priority claimed from US05/576,418 external-priority patent/US3965108A/en

1976-02-24 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1980-05-13 Application granted granted Critical

1980-05-13 Publication of CA1077484A publication Critical patent/CA1077484A/fr

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title abstract description 14
150000001412 amines Chemical class 0.000 title description 7
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 title description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
239000001257 hydrogen Substances 0.000 claims abstract description 49
150000003839 salts Chemical class 0.000 claims abstract description 22
150000002431 hydrogen Chemical class 0.000 claims abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims description 49
238000000034 method Methods 0.000 claims description 45
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
-1 dimethylaminopropyl Chemical group 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 15
125000003282 alkyl amino group Chemical group 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 abstract description 19
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 5
229910052757 nitrogen Inorganic materials 0.000 abstract description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
239000003874 central nervous system depressant Substances 0.000 abstract description 2
YMHQNVGWFTZOAO-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine-6-carboxylic acid Chemical class OC(=O)C1=CN=C2SC=NC2=C1 YMHQNVGWFTZOAO-UHFFFAOYSA-N 0.000 abstract 1
125000004494 ethyl ester group Chemical group 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 21
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
239000002253 acid Substances 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 13
239000000203 mixture Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
GKCNAXFKWLOVMQ-UHFFFAOYSA-N ethyl 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(Cl)C([N+]([O-])=O)=C1Cl GKCNAXFKWLOVMQ-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
YFRBFGUUUDQBMZ-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound OC(=O)C1=CN=C2SN=NC2=C1 YFRBFGUUUDQBMZ-UHFFFAOYSA-N 0.000 description 5
229940086542 triethylamine Drugs 0.000 description 5
RIMQELJEDBHDQZ-UHFFFAOYSA-N 2-nitronicotinic acid Chemical compound OC(=O)C1=CC=CN=C1[N+]([O-])=O RIMQELJEDBHDQZ-UHFFFAOYSA-N 0.000 description 4
NKDHMPWNRGPUSS-UHFFFAOYSA-N 4,6-dichloro-2-methyl-5-nitropyridine-3-carboxylic acid Chemical compound CC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=C1C(O)=O NKDHMPWNRGPUSS-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 3
QGKUVJPQLXSHQZ-UHFFFAOYSA-N 2-methyl-5-nitronicotinic acid Chemical compound CC1=NC=C([N+]([O-])=O)C=C1C(O)=O QGKUVJPQLXSHQZ-UHFFFAOYSA-N 0.000 description 3
HNTZKNJGAFJMHQ-UHFFFAOYSA-N 2-methylpyridine-3-carboxylic acid Chemical compound CC1=NC=CC=C1C(O)=O HNTZKNJGAFJMHQ-UHFFFAOYSA-N 0.000 description 3
BPEGUEGDAFCUCO-UHFFFAOYSA-N 4-(butylamino)-2-methyl-5-nitro-6-sulfanylidene-1h-pyridine-3-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC(S)=C1[N+]([O-])=O BPEGUEGDAFCUCO-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
239000002775 capsule Substances 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
PCADNOHSEZUSKN-UHFFFAOYSA-N ethyl 4-(butylamino)-6-chloro-2-methyl-5-nitropyridine-3-carboxylate Chemical compound CCCCNC1=C(C(=O)OCC)C(C)=NC(Cl)=C1[N+]([O-])=O PCADNOHSEZUSKN-UHFFFAOYSA-N 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
235000001968 nicotinic acid Nutrition 0.000 description 3
239000011664 nicotinic acid Substances 0.000 description 3
229910052979 sodium sulfide Inorganic materials 0.000 description 3
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 3
241000894007 species Species 0.000 description 3
239000003826 tablet Substances 0.000 description 3
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
TZAGBVHIUUFVCJ-UHFFFAOYSA-N 2047-49-6 Chemical compound OC(=O)C1=CN=CC([N+]([O-])=O)=C1 TZAGBVHIUUFVCJ-UHFFFAOYSA-N 0.000 description 2
HYNYFTRLQSLLHK-UHFFFAOYSA-N 4-(butylamino)-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC(Cl)=C1[N+]([O-])=O HYNYFTRLQSLLHK-UHFFFAOYSA-N 0.000 description 2
WUTYSRIKZCQXDN-UHFFFAOYSA-N 5-amino-4-(butylamino)-2-methyl-6-sulfanylidene-1h-pyridine-3-carboxylic acid Chemical compound CCCCNC1=C(N)C(S)=NC(C)=C1C(O)=O WUTYSRIKZCQXDN-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000006186 oral dosage form Substances 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
150000002905 orthoesters Chemical class 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000002335 preservative effect Effects 0.000 description 2
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
WVURJONRLJYKCL-UHFFFAOYSA-N 2-methyl-6-sulfanylidene-1h-pyridine-3-carboxylic acid Chemical compound CC=1NC(=S)C=CC=1C(O)=O WVURJONRLJYKCL-UHFFFAOYSA-N 0.000 description 1
ZMOVNBGEVRHQBL-UHFFFAOYSA-N 2-methyl-[1,3]thiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound OC(=O)C1=CN=C2SC(C)=NC2=C1 ZMOVNBGEVRHQBL-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZSBCDJUIVXNNTK-UHFFFAOYSA-N 4-[3-(dimethylamino)propylamino]-2-methyl-5-nitro-6-sulfanylidene-1h-pyridine-3-carboxylic acid Chemical compound CN(C)CCCNC=1C(C(O)=O)=C(C)NC(=S)C=1[N+]([O-])=O ZSBCDJUIVXNNTK-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
RACBBQGRLDTXOA-UHFFFAOYSA-N 4-amino-6-chloro-2-methyl-5-nitropyridine-3-carboxylic acid Chemical compound CC1=NC(Cl)=C([N+]([O-])=O)C(N)=C1C(O)=O RACBBQGRLDTXOA-UHFFFAOYSA-N 0.000 description 1
QJLHSJRQOWSNMD-UHFFFAOYSA-N 4-hydroxy-6-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CNC(O)=CC1=O QJLHSJRQOWSNMD-UHFFFAOYSA-N 0.000 description 1
VTSUEPUECVKWOS-UHFFFAOYSA-N 5-methyl-7-(propan-2-ylamino)thiadiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound CC(C)NC1=C(C(O)=O)C(C)=NC2=C1N=NS2 VTSUEPUECVKWOS-UHFFFAOYSA-N 0.000 description 1
ICCSFRIBNLHVBL-UHFFFAOYSA-N 7-(butylamino)-2,5-dimethyl-[1,3]thiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC2=C1N=C(C)S2 ICCSFRIBNLHVBL-UHFFFAOYSA-N 0.000 description 1
JSFVKYPVDFYSMV-UHFFFAOYSA-N 7-(butylamino)-5-methyl-[1,3]thiazolo[4,5-b]pyridine-6-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC2=C1SC=N2 JSFVKYPVDFYSMV-UHFFFAOYSA-N 0.000 description 1
PEBHKVYNVRXPDE-UHFFFAOYSA-N 7-(butylamino)-5-methyl-[1,3]thiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC2=C1N=CS2 PEBHKVYNVRXPDE-UHFFFAOYSA-N 0.000 description 1
YYNHWBUNEUIKCG-UHFFFAOYSA-N 7-(butylamino)-5-methylthiadiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound CCCCNC1=C(C(O)=O)C(C)=NC2=C1N=NS2 YYNHWBUNEUIKCG-UHFFFAOYSA-N 0.000 description 1
SBQOXBBEGFWYSF-UHFFFAOYSA-N 7-(ethylamino)-5-methyl-[1,3]thiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound CCNC1=C(C(O)=O)C(C)=NC2=C1N=CS2 SBQOXBBEGFWYSF-UHFFFAOYSA-N 0.000 description 1
BOLWRQMCBRULLR-UHFFFAOYSA-N 7-[3-(dimethylamino)propylamino]-2,5-dimethyl-[1,3]thiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound CN(C)CCCNC1=C(C(O)=O)C(C)=NC2=C1N=C(C)S2 BOLWRQMCBRULLR-UHFFFAOYSA-N 0.000 description 1
NZERXBCRRWABKS-UHFFFAOYSA-N 7-amino-5-methyl-[1,3]thiazolo[5,4-b]pyridine-6-carboxylic acid Chemical compound NC1=C(C(O)=O)C(C)=NC2=C1N=CS2 NZERXBCRRWABKS-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010018691 Granuloma Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010023232 Joint swelling Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
206010042674 Swelling Diseases 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
229940022663 acetate Drugs 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
229960004782 chlordiazepoxide Drugs 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000002497 edematous effect Effects 0.000 description 1
WUKXMLVJZDYSOR-UHFFFAOYSA-N ethyl 4-amino-6-chloro-2-methyl-5-nitropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C(Cl)C([N+]([O-])=O)=C1N WUKXMLVJZDYSOR-UHFFFAOYSA-N 0.000 description 1
QVVZZSDZBJQNTB-UHFFFAOYSA-N ethyl 4-hydroxy-2-methyl-5-nitro-6-oxo-1h-pyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(O)=C([N+]([O-])=O)C1=O QVVZZSDZBJQNTB-UHFFFAOYSA-N 0.000 description 1
LRPYUPUPHFABSE-UHFFFAOYSA-N ethyl 7-amino-5-methyl-[1,3]thiazolo[5,4-b]pyridine-6-carboxylate Chemical compound CCOC(=O)C1=C(C)N=C2SC=NC2=C1N LRPYUPUPHFABSE-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
RXCVUXLCNLVYIA-UHFFFAOYSA-N orthocarbonic acid Chemical compound OC(O)(O)O RXCVUXLCNLVYIA-UHFFFAOYSA-N 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
230000009772 tissue formation Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA246,424A 1975-03-05 1976-02-24 Derives amino des acides thiazolo (5,4-b) pyridine-6-carboxyliques et de leurs esters Expired CA1077484A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/555,512 US3953461A (en)	1975-03-05	1975-03-05	Amino derivatives of thiazolo[5,4-b]pyridine-6-carboxylic acids and esters
US05/576,418 US3965108A (en)	1975-05-12	1975-05-12	Amino derivatives of [1,2,3]thiadiazolo(5,4-b) pyridine-6-carboxylic acids and esters

Publications (1)

Publication Number	Publication Date
CA1077484A true CA1077484A (fr)	1980-05-13

Family

ID=27070910

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA246,424A Expired CA1077484A (fr)	1975-03-05	1976-02-24	Derives amino des acides thiazolo (5,4-b) pyridine-6-carboxyliques et de leurs esters

Country Status (5)

Country	Link
JP (1)	JPS51113894A (fr)
CA (1)	CA1077484A (fr)
DE (1)	DE2609009A1 (fr)
FR (1)	FR2302738A1 (fr)
GB (1)	GB1539914A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE0301373D0 (sv) *	2003-05-09	2003-05-09	Astrazeneca Ab	Novel compounds

1976
- 1976-02-24 CA CA246,424A patent/CA1077484A/fr not_active Expired
- 1976-03-04 DE DE19762609009 patent/DE2609009A1/de active Pending
- 1976-03-04 GB GB877176A patent/GB1539914A/en not_active Expired
- 1976-03-05 JP JP51024548A patent/JPS51113894A/ja active Pending
- 1976-03-05 FR FR7606353A patent/FR2302738A1/fr active Granted

Also Published As

Publication number	Publication date
DE2609009A1 (de)	1976-09-16
GB1539914A (en)	1979-02-07
FR2302738A1 (fr)	1976-10-01
FR2302738B1 (fr)	1979-08-24
JPS51113894A (en)	1976-10-07

Legal Events

Date	Code	Title	Description
1997-05-13	MKEX	Expiry

Publication	Publication Date	Title
DE69716810T2 (de)	2003-02-27	2,3-Disubstituierte-(5,6)-heteroarylkondensierte-pyrimidin-4-one
US4808594A (en)	1989-02-28	Imidopyridines useful in therapy
US4684727A (en)	1987-08-04	Zwitterionic 1,8-naphthyridine and pyrazino[2,3-b]pyridine containing compounds useful as anti-allergic, anti-inflammatory and cycloprotective agents
JPH02191281A (ja)	1990-07-27	新規チエノ―トリアゾロ―１，４―ジアゼピノ―２―カルボン酸
US3993656A (en)	1976-11-23	1,8-Naphthyridine compounds
EP0119774B1 (fr)	1987-06-24	Pyrazolopyridines anti-inflammatoires
UCHIKAWA et al.	1996	In vivo biological activity of antioxidative aminothiazole derivatives.
JPH0313235B2 (fr)	1991-02-22
DE3533331A1 (de)	1987-03-26	Pyridothiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
KR870001144B1 (ko)	1987-06-11	삼환 옥스인돌 카복스아미드 유도체의 제조방법
EP0580637A1 (fr)	1994-02-02	DERIVES D'IMIDAZO(4,5-c)PYRIDO, LEURS PROCEDE ET INTERMEDIAIRES DE PREPARATION, ET COMPOSITION PHARMACEUTIQUES LES CONTENANT
US4996213A (en)	1991-02-26	Derivatives of 4-amino 3-carboxy naphthyridines and their pharmaceutical compositions
CA1054600A (fr)	1979-05-15	Derives amino d'imidazo (4,5-b) pyridines
US4124587A (en)	1978-11-07	4-Hydroxy-3-sulfinyl-quinolin-2(1H)-ones
JPS59137469A (ja)	1984-08-07	複素環式化合物，その製法およびそれらを含有する中枢神経系薬物
US4544655A (en)	1985-10-01	Antiinflammatory, analgesic, and antirheumatic 4-hydroxy-2-methyl-n-(2-pyridyl)-6-trifluoromethyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide, corresponding compositions, and 3-carboxylic acid lower alkyl ester intermediates
CA1077484A (fr)	1980-05-13	Derives amino des acides thiazolo (5,4-b) pyridine-6-carboxyliques et de leurs esters
AU663017B2 (en)	1995-09-21	Chemical compounds
CA1050983A (fr)	1979-03-20	Derives amines des acides pyrido(2,3-b) pyrazine carboxyliques et de leurs esters
US3953461A (en)	1976-04-27	Amino derivatives of thiazolo[5,4-b]pyridine-6-carboxylic acids and esters
EP0193329A2 (fr)	1986-09-03	Pyrazolopyridines, leur préparation et compositions pharmaceutiques les contenant
CH629209A5 (en)	1982-04-15	Process for preparing penicillin derivatives
CA1050027A (fr)	1979-03-06	Derives d'acides pyrazolo (3,4-b) thieno (2,3-d) pyridine carboxyliques-2
US4091219A (en)	1978-05-23	Amino derivatives of 1,2,3,4-tetrahydro-2-oxopyrido[2,3-b]-pyrazine carboxylic acids and esters
JPS6229585A (ja)	1987-02-07	エーテル化若しくはエステル化しうるジヒドロキシ基により位置２で置換された４―ｏｈキノリンカルボン酸の新規の誘導体、その製造方法、及び医薬としてのその使用